Asymmetric synthesis of tert-butyl (3R, 5S) 6-chloro-dihydroxyhexanoate with Lactobacillus kefir. 2005

Maya Amidjojo, and Ezequiel Franco-Lara, and Alessandro Nowak, and Hannes Link, and Dirk Weuster-Botz
Institute of Biochemical Engineering, Munich University of Technology, Boltzmannstrasse 15, 85748 Garching, Germany.

An efficient whole cell biotransformation process using Lactobacillus kefir was developed for the asymmetric synthesis of tert-butyl (3R, 5S) 6-chloro-dihydroxyhexanoate, a chiral building block for the HMG-CoA reductase inhibitor. The effects of buffer concentration, temperature, pH and oxygen on the asymmetric reduction were investigated in batch reactions. Improvements in final product concentration and yields of 153% (120 mM) and 79% (0.85 mol/mol) with respect to the batch-process were achieved in an optimised fed-batch process. The pure substrate tert-butyl-6-chloro-3,5-dioxohexanoate was dispersed as microdroplets into the reaction system. This resulted in a space-time yield of 4.7 mmol l(-1) h(-1). A diastereomeric excess of >99% was measured for (3R, 5S) and (3S, 5S) tert-butyl 6-chloro-dihydroxyhexanoate.

UI MeSH Term Description Entries
D007778 Lactobacillus A genus of gram-positive, microaerophilic, rod-shaped bacteria occurring widely in nature. Its species are also part of the many normal flora of the mouth, intestinal tract, and vagina of many mammals, including humans. Lactobacillus species are homofermentative and ferment a broad spectrum of carbohydrates often host-adapted but do not ferment PENTOSES. Most members were previously assigned to the Lactobacillus delbrueckii group. Pathogenicity from this genus is rare.
D010100 Oxygen An element with atomic symbol O, atomic number 8, and atomic weight [15.99903; 15.99977]. It is the most abundant element on earth and essential for respiration. Dioxygen,Oxygen-16,Oxygen 16
D002021 Buffers A chemical system that functions to control the levels of specific ions in solution. When the level of hydrogen ion in solution is controlled the system is called a pH buffer. Buffer
D002208 Caproates Derivatives of caproic acid. Included under this heading are a broad variety of acid forms, salts, esters, and amides that contain a carboxy terminated six carbon aliphatic structure. Hexanoates,Caproic Acid Derivatives,Caproic Acids,Hexanoic Acid Derivatives,Hexanoic Acids,Acid Derivatives, Caproic,Acid Derivatives, Hexanoic,Acids, Caproic,Acids, Hexanoic,Derivatives, Caproic Acid,Derivatives, Hexanoic Acid
D005285 Fermentation Anaerobic degradation of GLUCOSE or other organic nutrients to gain energy in the form of ATP. End products vary depending on organisms, substrates, and enzymatic pathways. Common fermentation products include ETHANOL and LACTIC ACID. Fermentations
D006863 Hydrogen-Ion Concentration The normality of a solution with respect to HYDROGEN ions; H+. It is related to acidity measurements in most cases by pH pH,Concentration, Hydrogen-Ion,Concentrations, Hydrogen-Ion,Hydrogen Ion Concentration,Hydrogen-Ion Concentrations
D001709 Biotechnology Body of knowledge related to the use of organisms, cells or cell-derived constituents for the purpose of developing products which are technically, scientifically and clinically useful. Alteration of biologic function at the molecular level (i.e., GENETIC ENGINEERING) is a central focus; laboratory methods used include TRANSFECTION and CLONING technologies, sequence and structure analysis algorithms, computer databases, and gene and protein structure function analysis and prediction. Biotechnologies
D001711 Biotransformation The chemical alteration of an exogenous substance by or in a biological system. The alteration may inactivate the compound or it may result in the production of an active metabolite of an inactive parent compound. The alterations may be divided into METABOLIC DETOXICATION, PHASE I and METABOLIC DETOXICATION, PHASE II.
D013237 Stereoisomerism The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed) Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D013696 Temperature The property of objects that determines the direction of heat flow when they are placed in direct thermal contact. The temperature is the energy of microscopic motions (vibrational and translational) of the particles of atoms. Temperatures

Related Publications

Maya Amidjojo, and Ezequiel Franco-Lara, and Alessandro Nowak, and Hannes Link, and Dirk Weuster-Botz
October 2018, Bioorganic chemistry,
Maya Amidjojo, and Ezequiel Franco-Lara, and Alessandro Nowak, and Hannes Link, and Dirk Weuster-Botz
January 2020, Bioprocess and biosystems engineering,
Maya Amidjojo, and Ezequiel Franco-Lara, and Alessandro Nowak, and Hannes Link, and Dirk Weuster-Botz
May 2017, Journal of agricultural and food chemistry,
Maya Amidjojo, and Ezequiel Franco-Lara, and Alessandro Nowak, and Hannes Link, and Dirk Weuster-Botz
May 2017, Biotechnology progress,
Maya Amidjojo, and Ezequiel Franco-Lara, and Alessandro Nowak, and Hannes Link, and Dirk Weuster-Botz
January 2020, Biotechnology progress,
Maya Amidjojo, and Ezequiel Franco-Lara, and Alessandro Nowak, and Hannes Link, and Dirk Weuster-Botz
February 2018, Bioresource technology,
Maya Amidjojo, and Ezequiel Franco-Lara, and Alessandro Nowak, and Hannes Link, and Dirk Weuster-Botz
November 2015, Applied microbiology and biotechnology,
Maya Amidjojo, and Ezequiel Franco-Lara, and Alessandro Nowak, and Hannes Link, and Dirk Weuster-Botz
May 2019, 3 Biotech,
Maya Amidjojo, and Ezequiel Franco-Lara, and Alessandro Nowak, and Hannes Link, and Dirk Weuster-Botz
November 2008, Acta crystallographica. Section E, Structure reports online,
Maya Amidjojo, and Ezequiel Franco-Lara, and Alessandro Nowak, and Hannes Link, and Dirk Weuster-Botz
November 2003, Organic & biomolecular chemistry,
Copied contents to your clipboard!